Windham County CT Homes for Sale

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  /39

  $500,000

  • 4 Beds
  • 2.5 Baths
  • 2,655 Sq Ft

  53 Colleen St, Danielson, CT 06239

  Welcome to this spacious Colonial, ideally situated on a corner lot in a quiet neighborhood in Killingly. Offering over 2,600 square feet of living space, this home features generously sized rooms, a flexible layout, and plenty of space to fit a variety of needs. The updated kitchen and bathrooms provide modern convenience, while the dining room fireplace adds warmth and character. An oversized

  

  Monique Frigon

  Toro Real Estate LLC

  53 Colleen St, Danielson, CT 06239
• 

  

  

  /34

  $249,999

  Open Fri 5PM - 7PM

  • 3 Beds
  • 1 Bath
  • 998 Sq Ft

  16 Franklin St, Putnam, CT 06260

  Charming farmhouse-style home filled with warmth, character, and timeless appeal! This inviting 3-bedroom offers cozy living with beautiful built-ins, tasteful updates, and move-in-ready convenience. Recent improvements include a 3y/o 50-year architectural roof, updated flooring, and a new hot water heater for added peace of mind. The fully fenced yard is the perfect size for easy maintenance

  

  Catherine Howard

  Berkshire Hathaway NE Prop.

  16 Franklin St, Putnam, CT 06260
• 

  

  

  /40

  $499,900

  Open Sat 1PM - 3PM

  • 2 Beds
  • 1.5 Baths
  • 2,428 Sq Ft

  6 Autumn Ridge, Windham, CT 06280

  Experience exceptional craftsmanship in this magnificent timber frame home, thoughtfully designed with quality, comfort, and energy efficiency in mind. The stunning great room features soaring ceilings and an open-concept layout that flows seamlessly into the dining area and custom kitchen, creating an ideal space for everyday living and entertaining. A cozy propane stove adds warmth and ambiance

  

  Rick Nassiff

  KW Legacy Partners

  6 Autumn Ridge, Windham, CT 06280
• 

  

  

  /40

  $350,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,438 Sq Ft

  60 Chaplin St, Chaplin, CT 06235

  Welcome to place where time truly is the most beautiful thing. There is a particular kind of feeling when you walk through a historic door like this. Maybe it's the hardwood plank floors that have held two centuries of footsteps. Maybe it's the way the morning light hits the windows on every home on Chaplin Street, a village so notable it's listed on the National Register of Historic Places.

  

  Stephen Daly

  KW Legacy Partners

  60 Chaplin St, Chaplin, CT 06235
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  /38

  $625,000

  $21K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,478 Sq Ft

  429 New Sweden Rd, Woodstock, CT 06281

  Step back in time and discover the charm of this beautifully preserved 2,400 sq. ft. farmhouse, originally built in 1805. Rich in character and timeless appeal, this property offers the perfect blend of country living and modern convenience. Whether you dream of cultivating extensive gardens, raising animals, creating a self-sustaining homestead, or simply enjoying wide-open spaces, this property

  

  Elizabeth Scranton

  Kazantzis Real Estate, LLC

  429 New Sweden Rd, Woodstock, CT 06281
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  /38

  $449,900

  Open Sun 1PM - 3PM $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,988 Sq Ft

  39 Jefferson Dr, Danielson, CT 06239

  Don't miss the opportunity to own this beautiful home, thoughtfully designed for both comfortable everyday living and effortless entertaining. The spacious living room and formal dining room showcase gleaming hardwood floors, creating an inviting atmosphere for family and guests alike. The private primary suite features a walk-in closet and a full en-suite bath, offering a relaxing retreat at the

  

  Catherine Howard

  Berkshire Hathaway NE Prop.

  39 Jefferson Dr, Danielson, CT 06239
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  /38

  $789,000

  • 4 Beds
  • 2.5 Baths
  • 2,900 Sq Ft

  287 S Bear Hill Rd, Chaplin, CT 06235

  Set on 3.39 picturesque acres, this beautifully renovated property offers the perfect blend of luxury, function, and country charm-ideal for a mini farm, homestead, or private retreat. The heated and insulated 36x48 Morton barn features front and rear sliding barn doors, 2 horse stalls with potential for 6, 5 doggy doors, water, electric, skylights, and year-round water access-perfect for horses,

  

  Amy Rio

  Better Homes and Gardens Real Estate Executive Real Estate

  287 S Bear Hill Rd, Chaplin, CT 06235
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  /2

  $69,900

  • Land
  • 36,154 Sq Ft
  • $84,217 per Acre

  0 Collelo Ave Unit 24192702, Plainfield, CT 06354

  Bring your vision to life on this approved building lot. This parcel provides the flexibility to build a home that fits your lifestyle. This lot is a conveniently located near local amenities, 395 and the Rhode Island border.

  

  Mandy Gruslin

  Kazantzis Real Estate, LLC

  0 Collelo Ave Unit 24192702, Plainfield, CT 06354
• 

  

  /22

  $299,900

  • Land
  • 79 Acres
  • $3,796 per Acre

  00 Ide Perrin Rd, Woodstock, CT 06281

  On a private road surrounded by unspoiled natural beauty, this remarkable 79-acre property offers exceptional privacy and endless potential. Two brooks enhance the landscape - Lebanon Brook along the western boundary and Porter Pond Brook to the east. The land features a mix of wetlands and highlands, heavily wooded with abundant timber resources. Create your secluded homestead in the wilderness

  

  Catherine Howard

  Berkshire Hathaway NE Prop.

  00 Ide Perrin Rd, Woodstock, CT 06281
• 

  

  /40

  $659,900

  Open Sun 12PM - 1:30PM $40K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,301 Sq Ft

  38 Madison Ave, Thompson, CT 06277

  "Buyer's loss, your gain." Modern Luxury meets timeless design on a Cul-De-Sac in Thompson, CT! 38 Madison Ave was custom-built home in 2020 and set on nearly 2 private acres, this masterpiece redefines move-in ready. Located in a subdivision with underground utilities, this home offers an impeccable blend of curb appeal and sophisticated design. The Exquisite Interior Design boosts the heart of

  

  Lora Savage

  XSell Realty, LLC

  38 Madison Ave, Thompson, CT 06277
• 

  

  /7

  $325,000

  • Land
  • 17.62 Acres
  • $18,445 per Acre

  0 New Rd Unit 24172039, Thompson, CT 06277

  Discover the perfect blend of privacy, nature, and opportunity with this expansive 17.62 acre parcel in Thompson, CT. Tucked away off a shared driveway, this beautiful property offers a peaceful, wooded setting with rolling terrain, ideal for your dream home, private estate, or future investment. Surrounded by scenic New England landscape, the land features mature trees and road frontage along a

  

  Carol Ryniewicz

  CR Premier Properties

  0 New Rd Unit 24172039, Thompson, CT 06277
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  /9

  $285,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  37 Ruth St, Danielson, CT 06239

  Discover the potential in this fixer-upper featuring an ideal floor plan with spacious, flowing living areas and endless possibilities to make it your own. The open and functional layout offers great bones for a renovation project, with generously sized rooms, abundant natural light, and a seamless flow perfect for modern living and entertaining. Whether you're an investor, flipper, or buyer

  

  Elizabeth Scranton

  Kazantzis Real Estate, LLC

  37 Ruth St, Danielson, CT 06239
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  /18

  $145,000

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft

  65 R And r Park, Killingly, CT 06241

  Welcome to this beautifully maintained 3-bedroom, 2-bath park model home located in a desirable community in Killingly, CT. Offering an inviting open-concept floor plan, this home features a spacious living area that flows seamlessly into the kitchen and dining space, creating the perfect setting for everyday living and entertaining. Pride of ownership is evident throughout with its well-kept

  

  Michael Nugent

  RE/MAX Professional Associates

  65 R And r Park, Killingly, CT 06241
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  /24

  $595,000

  • Land
  • 100 Acres
  • $5,950 per Acre

  259 Quarry Rd, Woodstock, CT 06281

  Discover the possibilities on this exceptional 100-acre parcel on Quarry Road in scenic Woodstock, Connecticut. Boasting approximately 1,900 feet of road frontage, this expansive property offers a rare combination of privacy, natural beauty, and development potential. The current owner has already cleared three beautiful potential building sites, each positioned to take advantage of the

  

  Carol Ryniewicz

  CR Premier Properties

  259 Quarry Rd, Woodstock, CT 06281
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  /40

  $399,900

  Pre-Foreclosure

  • 5 Beds
  • 3.5 Baths
  • 2,836 Sq Ft

  394 Jerusalem Rd, Windham, CT 06280

  Timeless New England charm meets modern-day opportunity in this impressive 5-bedroom, 3.5-bath antique Colonial, where historic character and spacious living come together on a picturesque setting. Rich in original details, this one-of-a-kind home showcases wide-plank hardwood floors, stunning decorative fireplaces with ornate mantels, oversized windows, and classic architectural craftsmanship

  

  Amy Rio

  Better Homes and Gardens Real Estate Executive Real Estate

  394 Jerusalem Rd, Windham, CT 06280
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  /8

  $99,900

  • Land
  • 2.17 Acres
  • $46,037 per Acre

  26 Bass Ln, Brooklyn, CT 06234

  Rare opportunity to build your dream home on over 2 acres of beautiful, mostly cleared land! It's becoming increasingly difficult to find high, dry, level parcels like this that are ready for your vision. A survey will be available on July 7th. Offering approximately 250 feet of road frontage on Happy Lane, this private interior lot is shared by only two neighboring homes, providing exceptional

  

  Catherine Howard

  Berkshire Hathaway NE Prop.

  26 Bass Ln, Brooklyn, CT 06234
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  /39

  $674,000

  $16K PRICE DROP Pre-Foreclosure

  • 3 Beds
  • 2.5 Baths
  • 2,626 Sq Ft

  23 Senexet Rd, Woodstock, CT 06281

  Welcome to this stunning 2022-built Colonial set on 2.42 private acres in desirable Woodstock! Tucked back from the road and surrounded by nature, this beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of modern comfort and peaceful country living. Step inside to an inviting open-concept layout featuring gleaming hardwood floors, recessed lighting, and abundant natural

  

  Carol Ryniewicz

  CR Premier Properties

  23 Senexet Rd, Woodstock, CT 06281
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  /39

  $850,000

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft

  50 Swedetown Rd, Pomfret Center, CT 06259

  Nestled on 6.22 private acres, this exceptional Colonial offers the perfect blend of country living, modern updates, & equestrian amenities. Featuring 3 bedrooms, 2.5 baths, and approximately 2,080 square feet of living space, this well-maintained home is designed for both comfort and functionality. The remodeled kitchen (2019) is the heart of the home, featuring granite countertops, quality

  

  Carol Ryniewicz

  CR Premier Properties

  50 Swedetown Rd, Pomfret Center, CT 06259
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  /10

  $225,000

  • Land
  • 3.72 Acres
  • $60,484 per Acre

  80 Averill Rd, Pomfret, CT 06259

  Approved, shovel ready Commercial Building Site. Part of a 15.9 acre 3 Lot approved subdivision. This is Lot #3.04 the entrance is on Averill Rd It has 3.72 Acres. Engineering plans will accommodate a 5000SF building. Just off US Route 44.Shared driveway access with Commercial Property owned by Centerville Bank. Zoned Village Commercial. Ideal for Retail Centers & Strip Malls. Drive-Thru,

  

  Mary Collins

  Berkshire Hathaway NE Prop.

  80 Averill Rd, Pomfret, CT 06259
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  /11

  $79,700

  • Land
  • 1.92 Acres
  • $41,510 per Acre

  36 Olde Meadow Rd, Woodstock, CT 06281

  Rare opportunity to secure the last premium homesite in one of Woodstock's most desirable areas, Eastwood Estates. This approved building lot is being offered as part of a custom home package with a local established builder. It is not being offered for sale as "land only" and requires a build contract with the designated builder, PMR Home Design and Expansion. Buyers may choose from thoughtfully

  

  Tina Lajoie

  Signature Properties of N.E.

  36 Olde Meadow Rd, Woodstock, CT 06281
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  /40

  $599,000

  $26K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,768 Sq Ft

  244 Paine Rd, Pomfret, CT 06259

  Discover the best of country living on 2.35 private acres in desirable Pomfret, where a quality-built custom Colonial offers space, comfort, and a peaceful lifestyle. Built by Woodstock Builders Association, the home welcomes you with a bright front living room featuring refinished hardwood floors and French doors leading to the dining room. The updated kitchen offers quartz countertops, a cozy

  

  Mary Collins

  Berkshire Hathaway NE Prop.

  244 Paine Rd, Pomfret, CT 06259
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  /4

  $49,000

  • Land
  • 12,632 Sq Ft
  • $168,966 per Acre

  90 Serwan Ave, Windham, CT 06226

  This nice residential lot sits on the edge of Mansfield and Windham. This property offers an opportunity to secure residential land in an established neighborhood with essential utilities accessible. Zoning: R-4 (Residential) Utilities: Public water and public sewer are available in the street; electricity and cable are also accessible at the site. Taxes are $109 (2025). Situated in a residential

  

  Sharon Watson Stokland

  List N Show LLC

  90 Serwan Ave, Windham, CT 06226
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  /2

  $39,900

  $10K PRICE DROP

  • Land
  • 1,742 Sq Ft
  • $997,500 per Acre

  24 Center St, Killingly, CT 06239

  Prime Commercial land in the heart of Danielson! Unlock the potential of this parcel located in the center of town. Be part of the growing town.

  

  Mandy Gruslin

  Kazantzis Real Estate, LLC

  24 Center St, Killingly, CT 06239
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  /38

  $529,000

  • 3 Beds
  • 2 Baths
  • 2,005 Sq Ft

  39 Fox Rd, Putnam, CT 06260

  Tucked away in desirable East Putnam in a park-like setting, this beautifully maintained split-level home offers 2,197 square feet of thoughtfully designed living space.The main level welcomes you with a spacious living room centered around a cozy gas fireplace, creating the perfect gathering space. The dining room flows into the well-appointed kitchen featuring a distinctive hammered copper

  

  Valerie MacNeil

  Kazantzis Real Estate, LLC

  39 Fox Rd, Putnam, CT 06260
• 

  

  /14

  $650,000

  • Land
  • 153 Acres
  • $4,248 per Acre

  0 Kozey Rd, Eastford, CT 06242

  Extraordinary 153-acre parcel nestled in the heart of Connecticut's scenic Last Green Valley, offering exceptional privacy and natural beauty. This remarkable property borders Natchaug State Forest, Yale Meyers Forest, and the historic Old Connecticut Path, placing thousands of acres of protected woodland at your doorstep. Rolling terrain, hardwoods, and abundant wildlife create a stunning

  

  Elizabeth Scranton

  Kazantzis Real Estate, LLC

  0 Kozey Rd, Eastford, CT 06242
• 

  

  /40

  $649,900

  • 6 Beds
  • 6 Baths
  • 4,134 Sq Ft

  9 E Franklin St, Danielson, CT 06239

  Welcome to 9 East Franklin St, where modern comfort meets thoughtful design in this beautifully rebuilt side by side two-family home. The owner's unit feels like a private retreat, offering 3 spacious bedrooms, 2 beautifully updated full baths with heated floors, a convenient half bath, and gleaming hardwood floors throughout. A new 2022 roof adds peace of mind along with the home being fully

  

  Patrick Farley

  Statewide Premier Prop. LLC

  9 E Franklin St, Danielson, CT 06239
• 

  

  /39

  $459,900

  Open Sun 10AM - 12PM

  • 3 Beds
  • 2.5 Baths
  • 1,962 Sq Ft

  41 Bunny Ln, Brooklyn, CT 06234

  Welcome home to this beautifully updated Cape-style home offering 3 bedrooms and 2.5 bathrooms. This move-in-ready home includes hardwood flooring, a spacious den with a cozy pellet stove, and thoughtful improvements throughout. Recent improvements provide peace of mind and exceptional value, including a 2022 roof, new furnace, new hybrid heat pump/water heater, new Mitsubishi mini-split systems

  

  Christine Costa

  Kazantzis Real Estate, LLC

  41 Bunny Ln, Brooklyn, CT 06234
• 

  

  /25

  $355,000

  $24K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  57 Beaver Dam Rd, Woodstock Valley, CT 06282

  Adorable year-round home on Lake Bunggee, ideally located across from a private beach with stunning lake views. The main level features vaulted ceilings and an open-concept layout connecting the living room, dining area, and kitchen. There are two bedrooms on the main floor, along with a finished room on the lower level for added space. Enjoy not only the beautiful lake views but also a private

  

  Carol Ryniewicz

  CR Premier Properties

  57 Beaver Dam Rd, Woodstock Valley, CT 06282
• 

  

  /10

  $249,900

  • Land
  • 25.7 Acres
  • $9,724 per Acre

  220 Plains Rd, Windham, CT 06280

  Wonderful potential development opportunity. Road frontage on 2 roads, approximately 1350' of frontage on Plains Rd., and approximately 450' of frontage on Anna Maria Ln., and existing cul-du-sac subdivision. Possible 7-8 lots subdivision to be created.

  

  Rick Nassiff

  KW Legacy Partners

  220 Plains Rd, Windham, CT 06280
• 

  

  /17

  $44,900

  • Land
  • 2.29 Acres
  • $19,607 per Acre

  79 Windham Center Rd, Windham, CT 06280

  Nice level lot in a great location, frontage on Windham Center Rd. (RT 203), to the left of #73 Windham Center Rd. This lot will convey with a right of way over it to provide access to the lot behind it at 77-R Windham Center Rd. Close to shopping, schools, and downtown Willimantic, offers the potential to make for the perfect pace for you to build the home of your dreams at an affordable price.

  

  Rick Nassiff

  KW Legacy Partners

  79 Windham Center Rd, Windham, CT 06280
• 

  

  /26

  $438,500

  • 3 Beds
  • 1 Bath
  • 1,222 Sq Ft

  44 Polly Ave, Danielson, CT 06239

  Completely renovated easy one level living awaits in this beautiful 3 bed 1 bath ranch. This home features beautiful hardwood floors, granite countertops, and a bright, updated interior throughout. The spacious open kitchen and living room create the perfect layout for everyday living and entertainment, offering an airy feel with plenty of room to gather. The oversized bathroom features a custom

  

  Mandy Gruslin

  Kazantzis Real Estate, LLC

  44 Polly Ave, Danielson, CT 06239
• 

  

  /17

  $69,500

  $16K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 592 Sq Ft

  69 Meadowside Rd, Woodstock, CT 06281

  Your seasonal escape is waiting at Meadowside of Woodstock - a private, gated 100-site co-op campground in Connecticut's Quiet Corner. Lot 69 features TWO structures: a 1999 40-foot Retreat park model with central air, new refrigerator, new deck, and new grill, PLUS a 12x16 log cabin on a concrete slab with electric fireplace and AC. Sleeps 6 total. Fully furnished including brand new sofa.

  

  Robbie Greene Santos

  RE/MAX One

  69 Meadowside Rd, Woodstock, CT 06281
• 

  

  /35

  $790,000

  $160K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 3,004 Sq Ft

  524 Wauregan Rd, Brooklyn, CT 06234

  Welcome to this exceptional, custom built brick home, set on a stunning piece of property where quality, craftsmanship, and timeless design come together beautifully. From the moment you step inside, you will appreciate the vaulted ceilings, open layout, and impressive mix of hardwood, marble and tile flooring. The heart of the home features a beautifully designed kitchen with quartz countertops,

  

  Mandy Gruslin

  Kazantzis Real Estate, LLC

  524 Wauregan Rd, Brooklyn, CT 06234
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  /38

  $524,900

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft

  321 Day St, Brooklyn, CT 06234

  Welcome to this beautiful 2019 Raised Ranch, offering the perfect blend of modern comfort and peaceful country living. This inviting home features 3 generously sized bedrooms, 2 full bathrooms, hardwood floors and central air. The heart of the home is the stunning kitchen, complete with granite countertops, a large center island, stainless steel appliances, and plenty of space for cooking,

  

  Christine Costa

  Kazantzis Real Estate, LLC

  321 Day St, Brooklyn, CT 06234
• 

  

  /7

  $39,900

  • Land
  • 4.2 Acres
  • $9,500 per Acre

  46 North Rd, Windham, CT 06280

  Great opportunity to own a lot of record at a great price, approx. 3.9-4.2 acres. Offered as raw land. No formal survey available, all soil testing and surveying to be done by the potential owner. Great location, North Rd. is Route 14, across from the Windham Center School.

  

  Rick Nassiff

  KW Legacy Partners

  46 North Rd, Windham, CT 06280
• 

  

  /5

  $225,000

  • Land
  • 3.86 Acres
  • $58,290 per Acre

  00 Mashamoquet Rd, Pomfret, CT 06259

  Approved, shovel ready Commercial Building Site. Engineering initial plans to accommodate a 5000SF building. Part of a 15.9 acre 3 Lot approved subdivision. This is Lot #3.02 It has 3.86 acres. Boarders the popular Airline State Park Trail in Back. It is directly on US Route 44. Just after the Commercial Property owned by Centerville Bank. Zoned Village Commercial. Ideal for Retail Centers &

  

  Mary Collins

  Berkshire Hathaway NE Prop.

  00 Mashamoquet Rd, Pomfret, CT 06259
• 

  /2

  $299,900

  • 6 Beds
  • 3 Baths
  • 2,700 Sq Ft

  14 Carey St, Willimantic, CT 06226

  Excellent opportunity to own a spacious 2-family home with great flexibility for investors or owner-occupants. The first unit offers 2 bedrooms and 1 full bath, while the second unit features a generous 4-bedroom, 2-bath layout, providing plenty of space for larger households or strong rental potential. A 2-car garage adds valuable parking and storage, making this property even more attractive.

  

  Amy Rio

  Better Homes and Gardens Real Estate Executive Real Estate

  14 Carey St, Willimantic, CT 06226
• 

  

  /40

  $319,000

  • 3 Beds
  • 1 Bath
  • 1,510 Sq Ft

  58 Viens St, Putnam, CT 06260

  Back on Market! Buyers backed out because of payoff request is taking too long, should have it soon.|| Welcome to 58 Viens Street in Putnam, offering a fantastic opportunity to build equity and make it your own. This home features a flexible layout with two generously sized bedrooms upstairs and a first-floor primary bedroom, providing convenient living options for a variety of needs. Inside,

  

  Kostas Travisano

  Sailpoint Property Group

  58 Viens St, Putnam, CT 06260
• 

  

  /40

  $525,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,284 Sq Ft

  30 Grant Hill Rd, Brooklyn, CT 06234

  Custom passive solar Contemporary set on 5+ private acres surrounded by natural beauty and peaceful scenery. A 5-year-young sunroom with tile flooring offers flexible space for relaxing, gardening, or enjoying year-round views of the landscape. Step outside to the spacious deck, ideal for outdoor dining or quiet mornings overlooking the tranquil setting. The inviting living room features a newer

  

  Mary Collins

  Berkshire Hathaway NE Prop.

  30 Grant Hill Rd, Brooklyn, CT 06234
• 

  

  /9

  $34,900

  • Land
  • 1.95 Acres
  • $17,897 per Acre

  77-R Windham Center Rd, Windham, CT 06280

  Delightful lot of record, a rear lot that will convey with a right of way over 79 Windham Rd. A great opportunity at a great price. This lot offers wonderful privacy, in a central location, close to shopping, schools, recreation and more!

  

  Rick Nassiff

  KW Legacy Partners

  77-R Windham Center Rd, Windham, CT 06280

Showing Results 1 - 40, Page 1 of 8